Anwulignan

Details

• Internal ID: 54b6cffc-68f0-47f3-b53a-781bd63a3dde
• Taxonomy: Lignans, neolignans and related compounds > Dibenzylbutane lignans
• IUPAC Name: 4-[4-(1,3-benzodioxol-5-yl)-2,3-dimethylbutyl]-2-methoxyphenol
• SMILES (Canonical): CC(CC1=CC2=C(C=C1)OCO2)C(C)CC3=CC(=C(C=C3)O)OC
• SMILES (Isomeric): CC(CC1=CC2=C(C=C1)OCO2)C(C)CC3=CC(=C(C=C3)O)OC
• InChI: InChI=1S/C20H24O4/c1-13(8-15-4-6-17(21)19(10-15)22-3)14(2)9-16-5-7-18-20(11-16)24-12-23-18/h4-7,10-11,13-14,21H,8-9,12H2,1-3H3
• InChI Key: QDDILOVMGWUNGD-UHFFFAOYSA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₄
• Molecular Weight: 328.40 g/mol
• Exact Mass: 328.16745924 g/mol
• Topological Polar Surface Area (TPSA): 47.90 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 4.19
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

• Calophyn
• 4-[4-(1,3-Benzodioxol-5-yl)-2,3-dimethylbutyl]-2-methoxyphenol
• (+)-Anwulignan;Anwuligan
• rel-4-[(2R,3R)-4-(1,3-Benzodioxol-5-yl)-2,3-dimethylbutyl]-2-methoxyphenol
• Compound NP-013791
• QDDILOVMGWUNGD-UHFFFAOYSA-N
• AKOS040738922
• FT-0696054
• FT-0697283
• 4-[4-(1,3-benzodioxol-5-yl)-2,3-dimethyl-butyl]-2-methoxy-phenol
• 4-[4-(2H-1,3-benzodioxol-5-yl)-2,3-dimethylbutyl]-2-methoxyphenol
• 4-((2S,3R)-4-(benzo[d][1,3]dioxol-5-yl)-2,3-dimethylbutyl)-2-methoxyphenol
• Phenol, 4-[4-(1,3-benzodioxol-5-yl)-2,3-dimethylbutyl]-2-methoxy-, [S-(R*,S*)]-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9844	98.44%
Caco-2	+	0.8619	86.19%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.6712	67.12%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9289	92.89%
OATP1B3 inhibitior	+	0.8979	89.79%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7568	75.68%
P-glycoprotein inhibitior	+	0.6925	69.25%
P-glycoprotein substrate	-	0.9070	90.70%
CYP3A4 substrate	-	0.5949	59.49%
CYP2C9 substrate	-	0.6107	61.07%
CYP2D6 substrate	+	0.4019	40.19%
CYP3A4 inhibition	+	0.8577	85.77%
CYP2C9 inhibition	+	0.7817	78.17%
CYP2C19 inhibition	+	0.7491	74.91%
CYP2D6 inhibition	+	0.6198	61.98%
CYP1A2 inhibition	+	0.6447	64.47%
CYP2C8 inhibition	-	0.6777	67.77%
CYP inhibitory promiscuity	+	0.7377	73.77%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9508	95.08%
Carcinogenicity (trinary)	Non-required	0.4352	43.52%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.8475	84.75%
Skin irritation	-	0.7823	78.23%
Skin corrosion	-	0.9622	96.22%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9136	91.36%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	+	0.5875	58.75%
skin sensitisation	-	0.7482	74.82%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	-	0.7237	72.37%
Acute Oral Toxicity (c)	III	0.6514	65.14%
Estrogen receptor binding	+	0.7635	76.35%
Androgen receptor binding	+	0.7299	72.99%
Thyroid receptor binding	+	0.5960	59.60%
Glucocorticoid receptor binding	+	0.6263	62.63%
Aromatase binding	+	0.6051	60.51%
PPAR gamma	+	0.7029	70.29%
Honey bee toxicity	-	0.9130	91.30%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5149	51.49%
Fish aquatic toxicity	+	0.9924	99.24%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.34%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.77%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.78%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.36%	96.77%
CHEMBL2581	P07339	Cathepsin D	95.53%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.71%	92.62%
CHEMBL3492	P49721	Proteasome Macropain subunit	91.02%	90.24%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.33%	99.17%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	89.15%	99.15%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.77%	85.14%
CHEMBL4208	P20618	Proteasome component C5	88.08%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.55%	95.89%
CHEMBL2535	P11166	Glucose transporter	87.33%	98.75%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.89%	89.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.53%	86.33%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	84.19%	94.80%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.10%	95.56%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	82.94%	93.24%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.91%	89.50%
CHEMBL1255126	O15151	Protein Mdm4	81.23%	90.20%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	80.82%	82.67%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.49%	94.00%

Plants that contains it

• Iryanthera lancifolia
• Leucas aspera
• Machilus thunbergii
• Magnolia ovata
• Myristica argentea
• Myristica fragrans
• Saururus chinensis
• Schisandra chinensis
• Schisandra rubriflora
• Schisandra sphenanthera

Cross-Links

• PubChem: 13844304
• NPASS: NPC267990
• LOTUS: LTS0157636
• wikiData: Q105218755